Lead with the best version of yourself.

Knowing When to Hang Up Your Boots

by Jakob Hutter

Deciding when to hang up your boots is not as straightforward as some make it out to be, especially when someone has dedicated a larger part of their life to serving their country. 

People in the military come from diverse backgrounds and experiences, and the decision to continue or transition out of the military can be influenced by a wide range of factors, such as career opportunities, a sense of belonging, job security, and personal circumstances. Transitioning out can also be a challenging experience to adjusting back to civilian life, financial or health concerns, or finding employment.

F. Scott Fitzgerald describes this choice in his essay “The Crack-Up” saying, “The test of a first-rate intelligence is the ability to hold two opposed ideas in the mind at the same time, and still retain the ability to function.”

The decision to stay in or get out is one that many have considered over the course of their military service. A framework for making that decision  could be beneficial to those who understand that either decision has a follow-on impact that can affect not only themselves, but their family, loved ones, and their fellow service members. 

Therefore, I want to share my framework on five essential questions I consider when looking at my own career and knowing when it is time to hang up my own boots.

Are you happy?

Happiness looks different for everyone. I consider happiness to be simply being satisfied with life. When I am in this emotional state, I feel physically and mentally better, more productive, and I am more engaged with others. When it comes to being in the military, I have been overall satisfied with what I have had the opportunity to see and do since I began my military career. 

Many people would likely say something similar. According to Gallup last year, 88% of people said they were either “completely satisfied” or “somewhat satisfied” with their job. Some in the military may find this statistic surprising, especially if they find themselves trying to catch a few hours of sleep on the cold hard ground after a long day of training. When considering your happiness, think about your awareness of the current moment, what you are experiencing, and how it makes you feel.  

Is my family accepting of my continued service?

I married my wife in the summer of 2021, and with it came adding her as a consideration to my continued service. While being in the Army National Guard can mitigate some of the additional stresses that those on active duty face, including frequent moves and transitions, it can still bring unique challenges to any relationship. Her loving support in what I do is important to me, and I am grateful for it. With her by my side, I want to include her in my decisions that impact us both and consider her thoughts and feelings about my service.

If you believe in the phrase “families serve too” then it is important to have those crucial conversations with them to engage their thoughts on your military service. They should be part of your support system. In an environment that can bring complex challenges and opportunities to military service, support from loved ones should be seriously considered, as they are impacted in their own ways through your service.

Am I still healthy and fit to stay in?

Being physically fit and mentally tough is important to me as it enables me the ability to continue doing what I love to do. Being physically fit allows us the ability to accomplish our physical tasks while avoiding injury and maintaining our ability to deploy, and our mental health can sustain us through adversity.

The Army’s Holistic Health and Fitness (H2F) domains include physical, nutritional, mental, spiritual, and sleep readiness. With the overall goal of H2F to optimize Soldier readiness, being mindful of these components is important to be motivated and engaged with this process to know if I am still physically and mentally fit. Once I feel as though I am unable to maintain my own readiness, then it’s time to consider moving forward to mitigate being a hindrance to the success of the organization.

Am I serving myself or my Soldiers?

The advice that ‘you must own your career because nobody else will care more than you’ can be a helpful reminder. Taking ownership of your career is important, but the purpose behind this question is to understand if you are self-serving or selfless. For me, practicing servant leadership has been a way I take care of myself to better serve others. 

Robert Greenleaf, who coined the term “servant-leader” questions whether the roles of servant and leader can be used in harmony to serve others first over their own objectives. In practicing this philosophy, leaders can encourage ownership and trust in the team. In addition, through transparency and authenticity, servant leadership can best help motivate people to accomplish organizational goals.

Do I still find purpose in being in the military?

People join the military for a variety of reasons, but a commonality that exists in their commitment is that their service will bring a sense of purpose to their lives. Reflecting on our purpose in life is important, as 2 out of 3 people in the U.S. say the COVID-19 pandemic caused them to reconsider their purpose.

Doing what I love to do reminds me of the quote by Mark Twain, “Find a job you enjoy doing, and you will never have to work a day in your life.” I believe the work I am doing is more than just serving the guideposts throughout my career. Yet I want to be mindful not to overstay my welcome, so as long as I continue this journey with selfless service and integrity, I’ll find my purpose in continuing to serve.

Thoughtfully considering these questions is important as it considers your personal health, welfare, continued service, and the same for your loved ones. Leaving the military, I am sure, creates an intense major life transition that requires careful consideration and adjustments accordingly for the individual and their family.

If the answer to any of these questions is no or you think your serving is more about you than those you serve, then it’s time to explore your thought process that led to these responses. Discuss your thoughts with those that care about you. Assuming that the answer is that it is time to leave, then begin the process to transition out of the military, and enjoy the time you have left before you transition back to civilian life. There are also several organizations that support transitioning service members, to include: the Department of Veteran’s Affairs, Hire Heroes USA, and the Transition Assistance Program (TAP)

The decision to transition out of the military is a very personal one. For me, this framework has allowed me to reflect more deeply on why I chose to continue serving today. I am enjoying what I do and what I have done. I feel capable in my ability to continue serving others with the love and support of my family, so my answer to these questions is yes.  

CPT Jakob Hutter is a Kansas Army National Guard logistics officer currently serving as a Plans Officer for the 169th Combat Sustainment Support Battalion in Leavenworth, Kansas. In addition, he also serves as the Kansas FLIPL Program Manager. He has a Master of Science in Organizational Leadership and received his commission from Kansas State University in 2016. He is passionate about the science of Army logistics, the art of military leadership, and combining both to provide effective sustainment.